Phosphorus oxychloride → HCID 86721447, compound

HRID 869596Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:32]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][C:21]3[C:26](=O)[NH:25][C:24]([CH3:28])=[N:23][C:22]=3[CH2:29][CH2:30][CH3:31])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].P(Cl)(Cl)([Cl:35])=O>>[Cl:35][C:26]1[C:21]([CH2:20][C:18]2[CH:17]=[CH:16][C:10]3/[C:11](=[C:12](/[CH3:15])\[C:13]#[N:14])/[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:32][C:6]=4[O:7][CH2:8][C:9]=3[CH:19]=2)=[C:22]([CH2:29][CH2:30][CH3:31])[N:23]=[C:24]([CH3:28])[N:25]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 136348387HCID 136348387, compound

Product 1

HCID 86721447HCID 86721447, compoundYield 97.1%

Conditions

Temperature: 100 °C

Procedure

[step 3] (E)-2-{3-fluoro-8-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (960 mg, 2.23 mmol) obtained in step 2 was dissolved in phosphorus oxychloride (2.5 mL, 26.8 mmol), and the mixture was stirred at 100° C. for 2 hr. The mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v) to give (E)-2-{8-[(4-chloro-2-methyl-6-propylpyrimidin-5-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (970 mg, 97%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 v/v)

Sources & evidence

ORD record: ord-9f91c054ce194c5a8f7a906bb7ad465a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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